JP2004505071A - 光学的に純粋な（Ｓ）−β−ヒドロキシ−γ−ブチロラクトンの連続製造方法 - Google Patents

光学的に純粋な（Ｓ）−β−ヒドロキシ−γ−ブチロラクトンの連続製造方法 Download PDF

Info

Publication number: JP2004505071A
Authority: JP; Japan
Prior art keywords: carboxylic acid; catalyst; butyrolactone; hydroxy; acid derivative
Prior art date: 2000-07-27
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

JP2002515878A

Other languages

English (en)

Japanese (ja)

Inventor

クァク，ビョン−ソン

ジョン，キ−ナン

キム，テ−ユン

コ，キ−ホ

キム，ジン−ウン

キム，チュン−ギル

Original Assignee

エスケー　コーポレイション

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2000-07-27

Filing date

2001-01-17

Publication date

2004-02-19

2001-01-17 Application filed by エスケー　コーポレイション filed Critical エスケー　コーポレイション

2004-02-19 Publication of JP2004505071A publication Critical patent/JP2004505071A/ja

Status Pending legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 44
FUDDLSHBRSNCBV-UHFFFAOYSA-N (+)-(R)-3-hydroxytetrahydrofuranone Natural products OC1COC(=O)C1 FUDDLSHBRSNCBV-UHFFFAOYSA-N 0.000 title claims abstract description 26
FUDDLSHBRSNCBV-VKHMYHEASA-N (4s)-4-hydroxyoxolan-2-one Chemical compound O[C@@H]1COC(=O)C1 FUDDLSHBRSNCBV-VKHMYHEASA-N 0.000 title claims abstract description 26
238000010924 continuous production Methods 0.000 title description 7
239000003054 catalyst Substances 0.000 claims abstract description 49
150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 29
238000006243 chemical reaction Methods 0.000 claims abstract description 29
239000001257 hydrogen Substances 0.000 claims abstract description 21
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
238000004519 manufacturing process Methods 0.000 claims abstract description 17
229910000510 noble metal Inorganic materials 0.000 claims abstract description 17
230000008569 process Effects 0.000 claims abstract description 16
229910052809 inorganic oxide Inorganic materials 0.000 claims abstract description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
238000005984 hydrogenation reaction Methods 0.000 claims description 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 14
235000019441 ethanol Nutrition 0.000 claims description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 12
239000002904 solvent Substances 0.000 claims description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
239000000376 reactant Substances 0.000 claims description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 9
229910052707 ruthenium Inorganic materials 0.000 claims description 8
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 7
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 7
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 7
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 6
MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 6
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 6
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 6
239000000377 silicon dioxide Substances 0.000 claims description 6
-1 cyclic alcohols Chemical class 0.000 claims description 5
239000000203 mixture Substances 0.000 claims description 5
239000010948 rhodium Substances 0.000 claims description 5
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
239000004480 active ingredient Substances 0.000 claims description 4
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 4
235000011090 malic acid Nutrition 0.000 claims description 4
239000011973 solid acid Substances 0.000 claims description 4
150000001298 alcohols Chemical class 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
229910052741 iridium Inorganic materials 0.000 claims description 3
239000002808 molecular sieve Substances 0.000 claims description 3
229910052762 osmium Inorganic materials 0.000 claims description 3
229910052763 palladium Inorganic materials 0.000 claims description 3
229910052697 platinum Inorganic materials 0.000 claims description 3
229910052703 rhodium Inorganic materials 0.000 claims description 3
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 3
239000010457 zeolite Substances 0.000 claims description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
XFTRTWQBIOMVPK-YFKPBYRVSA-N Citramalic acid Natural products OC(=O)[C@](O)(C)CC(O)=O XFTRTWQBIOMVPK-YFKPBYRVSA-N 0.000 claims description 2
230000002378 acidificating effect Effects 0.000 claims description 2
XFTRTWQBIOMVPK-UHFFFAOYSA-N citramalic acid Chemical compound OC(=O)C(O)(C)CC(O)=O XFTRTWQBIOMVPK-UHFFFAOYSA-N 0.000 claims description 2
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 2
239000001630 malic acid Substances 0.000 claims description 2
150000007522 mineralic acids Chemical class 0.000 claims description 2
SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 2
239000011347 resin Substances 0.000 claims description 2
229920005989 resin Polymers 0.000 claims description 2
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
239000002253 acid Substances 0.000 claims 2
229910021536 Zeolite Inorganic materials 0.000 claims 1
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims 1
238000009776 industrial production Methods 0.000 abstract description 4
238000010586 diagram Methods 0.000 abstract 1
230000002349 favourable effect Effects 0.000 abstract 1
229910052736 halogen Inorganic materials 0.000 abstract 1
150000002367 halogens Chemical class 0.000 abstract 1
239000000243 solution Substances 0.000 description 10
239000000047 product Substances 0.000 description 7
YSEKNCXYRGKTBJ-BYPYZUCNSA-N dimethyl (2s)-2-hydroxybutanedioate Chemical compound COC(=O)C[C@H](O)C(=O)OC YSEKNCXYRGKTBJ-BYPYZUCNSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 5
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
230000008901 benefit Effects 0.000 description 4
230000009849 deactivation Effects 0.000 description 4
238000005470 impregnation Methods 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
238000000926 separation method Methods 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
150000001733 carboxylic acid esters Chemical class 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
230000001590 oxidative effect Effects 0.000 description 3
238000011084 recovery Methods 0.000 description 3
238000005245 sintering Methods 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
239000002699 waste material Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 2
150000007942 carboxylates Chemical class 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
238000011437 continuous method Methods 0.000 description 2
230000007423 decrease Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
229940116298 l- malic acid Drugs 0.000 description 2
238000011031 large-scale manufacturing process Methods 0.000 description 2
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
230000007774 longterm Effects 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
229910001220 stainless steel Inorganic materials 0.000 description 2
239000010935 stainless steel Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 description 1
DZAIOXUZHHTJKN-VKHMYHEASA-N 3S,4-dihydroxy-butyric acid Chemical compound OC[C@@H](O)CC(O)=O DZAIOXUZHHTJKN-VKHMYHEASA-N 0.000 description 1
QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 description 1
CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
230000003444 anaesthetic effect Effects 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
229960005261 aspartic acid Drugs 0.000 description 1
238000010923 batch production Methods 0.000 description 1
MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000002131 composite material Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000003912 environmental pollution Methods 0.000 description 1
230000032050 esterification Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
LOQFROBMBSKWQY-LURJTMIESA-N ethyl (3s)-4-cyano-3-hydroxybutanoate Chemical compound CCOC(=O)C[C@@H](O)CC#N LOQFROBMBSKWQY-LURJTMIESA-N 0.000 description 1
238000004880 explosion Methods 0.000 description 1
239000002360 explosive Substances 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000011194 food seasoning agent Nutrition 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
229910052738 indium Inorganic materials 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229940099690 malic acid Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000011027 product recovery Methods 0.000 description 1
238000010926 purge Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000004064 recycling Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
239000010409 thin film Substances 0.000 description 1
238000011282 treatment Methods 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
238000004876 x-ray fluorescence Methods 0.000 description 1

Images

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Furan Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)
Epoxy Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP2002515878A 2000-07-27 2001-01-17 光学的に純粋な（Ｓ）−β−ヒドロキシ−γ−ブチロラクトンの連続製造方法 Pending JP2004505071A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
KR1020000043472A KR100645665B1 (ko)	2000-07-27	2000-07-27	(ｓ)-베타-하이드록시-감마-부티로락톤의 연속 제조방법
PCT/KR2001/000071 WO2002010147A1 (en)	2000-07-27	2001-01-17	CONTINUOUS PROCESS FOR THE PRODUCTION OF OPTICALLY PURE (S)-β-HYDROXY-η-BUTYROLACTONE

Publications (1)

Publication Number	Publication Date
JP2004505071A true JP2004505071A (ja)	2004-02-19

Family

ID=36101293

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP2002515878A Pending JP2004505071A (ja)	2000-07-27	2001-01-17	光学的に純粋な（Ｓ）−β−ヒドロキシ−γ−ブチロラクトンの連続製造方法

Country Status (12)

Country	Link
US (1)	US6429319B1 (cs)
EP (1)	EP1309580B1 (cs)
JP (1)	JP2004505071A (cs)
KR (1)	KR100645665B1 (cs)
AT (1)	ATE303372T1 (cs)
CA (1)	CA2416707A1 (cs)
CZ (1)	CZ2003209A3 (cs)
DE (1)	DE60113126T2 (cs)
ES (1)	ES2248403T3 (cs)
HU (1)	HUP0301635A3 (cs)
PL (1)	PL364105A1 (cs)
WO (1)	WO2002010147A1 (cs)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR100710543B1 (ko) *	2001-07-07	2007-04-24	에스케이 주식회사	광학순도가 높은 순수한 (ｓ)-베타-하이드록시-감마-부티로락톤의 연속 제조방법
DE60226518D1 (de) *	2002-09-18	2008-06-19	Sk Holdings Co Ltd	Kontinuierliches verfahren zur herstellung von optisch reinem (s)-beta hydroxy- gamma-butyrolacton
US20090104669A1 (en) *	2006-03-02	2009-04-23	Oh-Jin Park	Method for Preparing (S)-3-Hydroxy-Gamma-Butyrolactone Using Hydrolase
EP1996987B1 (en)	2006-03-17	2018-10-31	iRobot Corporation	Robot confinement

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8618890D0 (en) *	1986-08-01	1986-09-10	Davy Mckee Ltd	Process
US4782167A (en) *	1987-01-23	1988-11-01	E. I. Du Pont De Nemours And Company	Process for preparing butyrolactones and butanediols
GB8809587D0 (en) *	1988-04-22	1988-05-25	Ucb Sa	Process for making gamma-butyrolactone
CA2049536C (en)	1991-05-13	1999-07-06	Rawle I. Hollingsworth	Process for the preparation of 3,4-dihydroxybutanoic acid and salts thereof
DE69225560T2 (de) *	1991-11-18	1998-11-12	Sagami Chem Res	Verfahren zur Herstellung von Lactonen
JP3194816B2 (ja) *	1993-06-30	2001-08-06	東ソー株式会社	ラクトン類の製造方法
KR950006154A (ko) *	1993-08-26	1995-03-20	박태성	지중변위 측정을 위한 측력감지장치
KR960008247A (ko) *	1994-08-01	1996-03-22	이진호	냉장고의 습기공급 장치
US5473104A (en)	1994-09-13	1995-12-05	Neurocrine Biosciences, Inc.	Process for the preparation of L-carnitine
JPH08141396A (ja) *	1994-11-28	1996-06-04	Mitsubishi Chem Corp	カルボン酸類の水素化触媒及び該触媒を用いたカルボン酸類の水素化方法
AU3515497A (en)	1996-07-29	1998-02-20	Warner-Lambert Company	Improved process for the synthesis of protected esters of (s)-3,4-dihydroxybutyric acid
US5808107A (en) *	1997-10-31	1998-09-15	Board Of Trustees Operating Michigan State University	Process for the preparation of hydroxy substituted gamma butyrolactones
JP3614367B2 (ja) *	1998-07-24	2005-01-26	サムスンファインケミカルズカンパニーリミテッド	光学的に純粋な（ｓ）−３，４−ジヒドロキシ酪酸誘導体の連続的な製造方法

2000
- 2000-07-27 KR KR1020000043472A patent/KR100645665B1/ko not_active Expired - Fee Related
2001
- 2001-01-17 WO PCT/KR2001/000071 patent/WO2002010147A1/en not_active Ceased
- 2001-01-17 HU HU0301635A patent/HUP0301635A3/hu unknown
- 2001-01-17 PL PL01364105A patent/PL364105A1/xx not_active Application Discontinuation
- 2001-01-17 DE DE60113126T patent/DE60113126T2/de not_active Expired - Fee Related
- 2001-01-17 EP EP01984416A patent/EP1309580B1/en not_active Expired - Lifetime
- 2001-01-17 AT AT01984416T patent/ATE303372T1/de not_active IP Right Cessation
- 2001-01-17 CA CA002416707A patent/CA2416707A1/en not_active Abandoned
- 2001-01-17 CZ CZ2003209A patent/CZ2003209A3/cs unknown
- 2001-01-17 ES ES01984416T patent/ES2248403T3/es not_active Expired - Lifetime
- 2001-01-17 JP JP2002515878A patent/JP2004505071A/ja active Pending
- 2001-01-22 US US09/767,668 patent/US6429319B1/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
ATE303372T1 (de)	2005-09-15
EP1309580B1 (en)	2005-08-31
KR20020010190A (ko)	2002-02-04
PL364105A1 (en)	2004-12-13
DE60113126D1 (de)	2005-10-06
EP1309580A1 (en)	2003-05-14
US6429319B1 (en)	2002-08-06
KR100645665B1 (ko)	2006-11-13
CZ2003209A3 (cs)	2003-05-14
CA2416707A1 (en)	2002-02-07
WO2002010147A1 (en)	2002-02-07
HUP0301635A3 (en)	2004-06-28
HUP0301635A2 (hu)	2003-08-28
ES2248403T3 (es)	2006-03-16
EP1309580A4 (en)	2004-02-04
US20020035275A1 (en)	2002-03-21
DE60113126T2 (de)	2006-06-22

Publication	Publication Date	Title
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